Glycine tert-butyl ester hydrochloride → HCID 67502849, compound

HRID 2176697Notes

Reaction equation

HRID 2176697 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.Cl.C([O:19][C:20](=[O:23])[CH2:21][NH2:22])(C)(C)C>>[ClH:1].[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:22][CH2:21][C:20]([OH:23])=[O:19])=[CH:3][CH:4]=[N:5]2)=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 2725036Glycine tert-butyl ester hydrochlorideHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 67502849HCID 67502849, compoundYield 80.1%

Conditions

Temperature
100 °C

Procedure

In a 100 mL round bottom flask were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (5.00 g, 25.7 mmol) and glycine tert-butyl ester hydrochloride (17.2 g, 103 mmol) in 50 mL of 2-BuOH then stirred and heated at 100° C. After 5 h the solvent based on LC-MS was removed by reduced pressure and then the solid was dissolved in 200 mL of HCl 1N and stirred at 60° C. overnight. After 10 h the reaction mixture based on LC-MS was cooled down to rt then 0° C. and the desired acid precipitate. Filtered the solid (3.97 g) then evaporated the aqueous solution and triturated in 75 mL of H2O at 0° C. then filter again and washed with 25 mL of H2O at 0° C. (1.58 g) to afforded total 2-(7-methoxy-1,5-naphthyridin-4-ylamino)acetic acid hydrochloride (5.55 g, 80.1% yield) as a tan solid. MS m/z=234.1 [M+1]+. Calc'd for C11H11N3O3: 233.1.

Workup

  1. customwas removed by reduced pressure
  2. dissolutionthe solid was dissolved in 200 mL of HCl 1N
  3. stirringstirred at 60° C. overnight
  4. waitAfter 10 h the reaction mixture based on LC-MS
  5. temperaturewas cooled down to rt
  6. custom0° C.
  7. filtrationFiltered the solid (3.97 g)
  8. customthen evaporated the aqueous solution
  9. customtriturated in 75 mL of H2O at 0° C.
  10. filtrationthen filter again
  11. washwashed with 25 mL of H2O at 0° C. (1.58 g)

Sources & evidence

ORD record
ord-9be0e743faf741ce88065783d8ec5296
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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